nafcillin
Also known as (2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, naphcillin, (2-ethoxy-1-naphthalenyl)penicillin, 6-(2-ethoxy-1-naphthamido)penicillanic acid, (2-ethoxy-1-naphthyl)penicillin
Nafcillin sodium is a narrow-spectrum, second-generation beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.
Chemical data
- Formula
- C21H22N2O5S
- Molecular weight
- 414.5 g/mol
- IUPAC name
- (2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
- InChIKey
- GPXLMGHLHQJAGZ-JTDSTZFVSA-N
- XLogP
- 2.9
- Polar surface area
- 121 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
1,061 papers~3 min read
Article
5 sectionsContents
- Indications
- Side-effects
- Interactions
- Mechanism of Action
- References
Nafcillin sodium is a narrow-spectrum, second-generation beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.
Nafcillin is considered therapeutically equivalent to oxacillin, although one retrospective study found greater rates of hypokalemia and acute kidney injury in patients taking nafcillin compared to patients taking oxacillin.